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Yes! I have done this several times. Often the arrival of a new baby reminds us how much we miss lost loved ones, and I have been asked to draw with this is mind before. It may even be possible to create a portrait where it looks like the person is holding a new baby, or a similar pose. Please get in touch to inquire about this and I will do my best to advise you on what is possible with the reference images you have.
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Unfortunately this isn't usually possible. When planning a piece, I usually take a lot of time trying different layouts until I'm confident that I have utilised the space properly and in a balanced, eye-pleasing way. This means that there usually isn't enough space to squeeze anything else onto the portrait, and if there was, it would most likely throw the entire thing off balance.
